Yahoo Annual Meeting Countdown (2 Days to Go!): Slim Pickens!

That sounds like something that would happen out on the back 40 of a Texas ranch that no one in the clan ever discusses in polite company.

Actually, losing about $50 million is also something moneymen like Pickens don’t like to talk about either, even if he is as rich as can be.

Of course, in dumping his 10 million shares so precipitously, Pickens’s parting shot showed exactly what Yahoo’s big weakness is as the company heads into its annual meeting this Friday: an increasingly depressed stock.

Indeed, because of Pickens’s departure as an investor, Yahoo (YHOO) shares dropped just below the dangerous $20 a share level yesterday to $19.71, not far off the $19.18 price that prompted Microsoft (MSFT) to attack in February.

Yahoo shares are now just holding onto the edge at $20.05 this morning.

This is perhaps Yahoo’s biggest external problem. While the stock has shown resilience of really dipping to the mid-teens, if the shares drop that far, Pickens will look attractive compared with the kind of vulture investors who will show up to pick at Yahoo.

While Yahoo’s assets add up to $20 or more per share on a cash basis, staying above this threshold has largely been predicated on the fact that investors imagine some deal, any deal, between Yahoo and Microsoft in the future.

Such a deal might be the right move, but investors should probably accept the fact that it might never happen and that Yahoo and Microsoft will keep their digital efforts solo.

That’s the trap Pickens wandered right into like a particularly clueless bear.

And while Pickens took aim at Yahoo CEO Jerry Yang at an editorial board meeting with the San Francisco Chronicle yesterday, noting, “I think that Yahoo management was pathetic,” the fault is entirely Pickens’s own in greedily following along with activist investor and longtime crony Carl Icahn.

Pickens had bought a pile of shares in May, after Icahn announced his intention to wage a proxy fight against Yahoo and force it into a sale of some sort to Microsoft.

One problem: Yahoo and Microsoft execs did not go along with the grand idea of enriching either Pickens or Icahn, who aren’t exactly digitally inclined.

That’s no negative really, except to say that the Internet space is not quite the same as oil or, really, most other industries yet.

Despite the struggles of Yahoo and Microsoft against the more powerful Google (GOOG), the Internet remains a fast-growing industry with many options.

In other words, not quite ripe enough for takeover artists’, well, pickin’.

Just as the atom bomb was the weapon that was supposed to render war obsolete, the Internet seems like capitalism’s ultimate feat of self-destructive genius, an economic doomsday device rendering it impossible for anyone to ever make a profit off anything again. It’s especially hopeless for those whose work is easily digitized and accessed free of charge.

— Author Tim Kreider on not getting paid for one’s work

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